Digital risks are a continuously developing and evolving aspect of conducting business in the modern world. As high-profile losses to organizations are incurred via data theft or loss, insurers have attempted to fill the gap by providing both digital-risk coverage in general corporate-liability policies and specialized insurance policies, such as cyber insurance. However, the traditional paradigm of insurance interpretation presents significant challenges to both insurer and insured when attempting to translate terminology to the digital realm. Can digital “risk” truly be adequately covered? If a coverage dispute gets litigated, courts must interpret the contract to determine whether a risk event was covered. In doing so, courts face tension between prioritizing party intent in interpreting such contract terms or prioritizing risk-shifting to protect third parties. This Note surveys such litigation by categorizing cases using four axes of digital risk and analyzing trends to ascertain whether a court’s priorities in interpreting such insurance can be predicted. Two solutions to remedy any interpretation issues are discussed, each with potential shortcomings and pitfalls.